Here is the 1999 MetroStars schedule. Please note that all times are ET and that the schedule is subject to change.
| Date | Opponent | Time (ET) |
| Sat. March 20 | at Miami | 8:00 p.m. |
| Sun. March 28 | Columbus | 1:00 p.m. |
| Sat. April 3 | D.C. United | 7:00 p.m. |
| Sun. April 11 | at Tampa Bay | 5:00 p.m. |
| Sun. April 25 | Tampa Bay | 1:00 p.m. |
| Sat. May 1 | Los Angeles | 7:00 p.m. |
| Sat. May 8 | at D.C. United | 4:00 p.m. |
| Sat. May 15 | Miami | 7:00 p.m. |
| Sat. May 22 | at Colorado | 9:00 p.m. |
| Sat. May 29 | New England | 7:00 p.m. |
| Sat. June 5 | Dallas | 7:00 p.m. |
| Sat. June 12 | Colorado | 7:00 p.m. |
| Sun. June 20 | at Kansas City | 1:00 p.m. |
| Sat. June 26 | at Columbus | 7:30 p.m. |
| Wed. June 30 | Tampa Bay | 7:00 p.m. |
| Sun. July 4 | at New England | 4:30 p.m. |
| Sat. July 10 | at Chicago | 8:30 p.m. |
| Sat. July 24 | Miami | 3:00 p.m. |
| Wed. Aug. 4 | at Dallas | 8:30 p.m. |
| Sat. Aug. 7 | at Miami | 7:30 p.m. |
| Wed. Aug. 11 | D.C. United | 7:00 p.m. |
| Sat. Aug. 14 | Kansas City | 7:00 p.m. |
| Wed. Aug. 18 | Columbus | 7:00 p.m. |
| Sat. Aug. 21 | at Los Angeles | 10:30 p.m. |
| Wed. Aug. 25 | New England | 7:00 p.m. |
| Sat. Aug. 28 | at San Jose | 10:30 p.m. |
| Sun. Sept. 5 | Chicago | 1:00 p.m. |
| Sun. Sept. 12 | at Columbus | 1:00 p.m. |
| Sat. Sept. 18 | at D.C. United | 7:30 p.m. |
| Wed. Sept. 22 | San Jose | 7:30 p.m. |
| Sat. Sept. 25 | at Tampa Bay | 7:00 p.m. |
| Sat. Oct. 2 | at New England | 7:30 p.m. |